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80 Chicago Trivia Questions, Answers, and Fun Facts

How much do you know about Chicago? This category is for trivia questions and answers related to Chicago (Geography). Each one is filled with fun facts and interesting information.
1 Chicago, Illinois is located at the south end of which of the five US Great Lakes?
Answer: Lake Michigan

Chicago hugs the southern shores of Lake Michigan, the second largest of the Great Lakes by volume and the fifth largest lake in the world. Often called "the third coast" because of its extensive shores and beaches, tourists can sail, choose from a host of cruises, tour the city architecture from the water, and even fish, kayak or speedboat.

There has been increasingly extreme and unpredictable weather on the lake due to global warming, and unfortunately in 2014 certain international companies were found to be dumping or spilling large amounts of pollutants into the water. There are, however, still plenty of safe and exciting things to do in Chicago's extensive waters.
    Your options: [ Lake Superior ] [ Great Bear Lake ] [ Lake Huron ] [ Lake Michigan ]
  From Quiz: Chicago! Popeye's Magical Pizza City of Champions
2 What well-known dictator donated the Balbo Monument, which was erected to commemorate the first transatlantic crossing of the Italian air force from Orbetello, Italy to Chicago, Illinois?
Answer: Benito Mussolini

The Balbo Monument was erected in 1933 during the World Exposition: A Century of Progress (1933-1934). The monument is composed of a 2000-year-old Ostian column, mounted on a travertine base, with the following inscription (rendered in both English and Italian):

"This column
twenty centuries old
erected on the shores of Ostia
port of Imperial Rome
to safeguard the fortunes and victories
of the Roman triremes
Fascist Italy by command of Benito Mussolini
presents to Chicago
exaltation symbol memorial
of the Atlantic Squadron led by Balbo
that with Roman daring flew across the ocean
in the eleventh year
of the Fascist era"

The use of a Roman column and decorative fasces bracketing the inscription on the monument are evidence of one of Mussolini's greatest desires; that is, Mussolini sought to prove that his Fascist regime was the rightful descendant of ancient Roman civilization. Therefore, he often found ways to link them together in an effort to increase the belief in the greatness of his Fascist regime.


Balbo Monument
Burnam Park
1550 S. Lakeshore Drive
Chicago, IL 60605

Website- Ostia: Harbor City in Rome
    Your options: [ Adolf Hitler ] [ Francisco Franco ] [ Benito Mussolini ] [ Giuseppe Garibaldi ]
  From Quiz: Windy City Wonders
3 Running beneath Chicago's Uptown neighborhood are tunnels. These tunnels are infamous for their use in the jazz age as an escape route for gangsters such as Al Capone. Under which Uptown destination can you find the entrance to these tunnels?
Answer: The Green Mill

One tunnel entrance can be found underneath the Green Mill tavern. The tunnels were not originally built for gangster use - they connected the tavern with its beer garden, located where the Uptown Theatre now stands. During the age of Prohibition, they were used both as an escape route for mobsters and as a hiding place for illicit alcohol.
    Your options: [ The Wilson "El" Station ] [ The Goldblatts Building ] [ The Green Mill ] [ Truman College ]
  From Quiz: Beneath Chicago
4 One of the most famous landmarks in Chicago, this fabled structure survived the Great Fire.
Answer: The Chicago Water Tower

This Gothic style artifice was constructed of limestone blocks and completed in 1869. It was the first American Water Landmark selected by the American Water Works Association.
    Your options: [ Water Tower Place ] [ The Chicago Water Tower ] [ Wrigley Field ] [ Field Museum of Natural History ]
  From Quiz: The Windy City
5 Who said "Da pleece aren't here to create disorder, They're here to preserve disorder".
Answer: Richard J. Daley

Mike Royko wrote a great book about Daley entitled "Boss".
    Your options: [ Richard J. Daley ] [ Len O'Connor ] [ Orlando Wilson ] [ Bozo The Clown ]
  From Quiz: My Kind Of Town, Chicago
6 The famous northside jazz bar was haunted by Hollywood stars and the ultimate gangster in Chicago. What is the name of this jazz bar?
Answer: The Green Mill

The Green Mill is one of the best joints to see live jazz six days a week in Chicago (sunday nights are Slam Poetry night). This century old joint hasn't changed a bit since the days of Al Capone and Fred Astaire. A must for jazz enthusiastes
  From Quiz: Absolute historic places in Chicago!
7 Which train line serves both Wrigley Field, the north side home of the Cubs, and US Cellular Park, the south side home of the White Sox?
Answer: Red

The Red line, formerly known as the State Street subway, runs from the northern edge of Chicago, about 7400 N, down to about 9500 S. Exit at Addison to catch the Cubs or at 35th for a Sox game. Incidentally, the name US Cellular Field is a new one in Chicago. Until this year, Sox park was named Comiskey Park, after Charles Comiskey, former owner of the team.
    Your options: [ Blue ] [ Red ] [ Brown ] [ Purple ]
  From Quiz: Riding the Rails on the CTA
8 Being settled near a US Great Lake enabled Chicago to become one of the largest and most prosperous cities in the world, in much part because of what?
Answer: Waterway transportation

Chicago's location at Lake Michigan allowed command of both inland and water transportation, so that abundant fur trade, coastal real estate speculation, an active shipping port, and ability to transport manufactured goods through the seaways and across the Great Lakes made Chicago a boom-town. Add to that a strong railroad, highway and air transportation business, with a heavy influx of immigrants by 1870, and Chicago fast became one of the largest cities in the world. It has exceled not only in industry and transportation, but in broadcasting, finance, higher education, medical training, culture and music.
  From Quiz: Chicago! Popeye's Magical Pizza City of Champions
9 The University of Chicago campus has a large, bulbous, bronze sculpture by Henry Moore. It marks the site where what scientific phenomenon was first developed and tested?
Answer: Nuclear reactor

The first nuclear reactor (Chicago Pile-1) was developed in Enrico Fermi's lab, which was located on a squash court beneath the west grandstand at Stagg Field. This nuclear reactor was used to generate the first controlled, self-sustaining nuclear reaction, even though the scientists weren't sure that the reaction could be stopped once initiated. The original Stagg Field is a mere memory, but Henry Moore's enigmatic sculpture serves as a poignant reminder of the Manhattan Project and the world-changing events ignited on December 02, 1942.


Nuclear Energy Statue
5651 S. Ellis Street
Chicago, IL. 60637

Website- Wikipedia
  From Quiz: Windy City Wonders
10 Completed in 1969, this 100-story steel and glass skyscraper is named after a famous American revolutionary.
Answer: The John Hancock Center

The John Hancock Center is a 100-story multifunctional structure. It houses 48 floors of apartments, 29 floors of offices, stores, a hotel, ice rink, radio and television stations, and a swimming pool. Its observation deck offers one of the best views of the lakefront and the Loop.
    Your options: [ The John G. Shedd Aquarium ] [ The John Hancock Center ] [ The Wrigley Building ] [ The Sears Tower ]
  From Quiz: The Windy City
11 Name the team: George "The Baron" Mitterwald, Mitch "Wild Thing" Williams and Dave "Kong" Kingman.
Answer: Da Cubs

The Cubbies have been breaking their fans' hearts annually since losing to Detroit in the 1945 World Series!
    Your options: [ Da Cubs ] [ Da Bears ] [ Da Sox ] [ Da Hawks ]
  From Quiz: My Kind Of Town, Chicago
12 The famous jazz saxaphonist Fred Anderson owns this jazz joint.
Answer: The Velvet Lounge

The Velvet Lounge is my favorite place to see true Chicago jazz artists do their thing. This place has a bar and a stage, but everything else is just plain. But the people that go to "the lounge" really don't care about pleasentries anyway. 2121 S. Indiana Ave
    Your options: [ Empty bottle ] [ Andy's Jazz Club ] [ The Velvet Lounge ] [ Pops for Champagne ]
  From Quiz: Absolute historic places in Chicago!
13 In 1871, most of Chicago was destroyed in the Great Chicago Fire. Out of the ashes citizens recreated the town, earning which nickname? Hint: "Phoenix" was already taken.
Answer: Second City

The recovery from the Great Chicago Fire of 1871 earned Chicago the nickname "Second City", because it rose again. Some argue it means "second to New York City". Chicago is also known as the "windy city", though the reason is unclear, as Chicago is no more breezy than many places. Early Cincinnati rivals may have named Chicago windy, as in, "full of hot air", or prone to bragging.

Other nicknames come from Carl Sandburg's "City of the Big Shoulders", Upton Sinclair's "The Jungle", and American cartoonist Elzie Segar who created Popeye. It is the City of Champions for sports fans, and well known for its delicious deep-dish pizza. President Barack Obama made his home there. President Ronald Reagan was born in a small village not so distant.
    Your options: [ City of Champions ] [ Sunny City ] [ The Jungle ] [ Second City ]
  From Quiz: Chicago! Popeye's Magical Pizza City of Champions
14 What Chicago landmark is located at 2325-2333 N. Clark Street, where two pharaohs stand guarding a gilded entryway?
Answer: Reebie Storage & Moving Company

In 1923, the Reebie Storage & Moving Company building was built by John and William Reebie. The Egyptian Revival design was inspired by the then-recent (1922) discovery of the tomb of King Tutankhamen by Howard Carter. The theme is also evidenced within, as the lobby is decorated with Egyptian columns, art glass windows, metalwork, and plaster castings. Most entertaining, though, are the entrance hieroglyphics, which when translated state, "I give protection to your furniture" and "Forever I work for all your regions in daylight and darkness".


Reebie Storage & Moving Company
2325-2333 N. Clark Street
Chicago, IL 60614
  From Quiz: Windy City Wonders
15 What major event in the history of science occurred in an underground racquetball court at the University of Chicago in 1942?
Answer: The first self-sustaining, synthetic nuclear reaction

The first man-made nuclear reactor, named Chicago Pile-1, was started in December of 1942 by Enrico Fermi and Leo Szilard. It was going to happen at the Argonne National Laboratory, but a labor strike resulted in the relocation of the event to an unceremonious gymnasium.

The reactor consisted of a stack of uranium and graphite blocks, controlled by rods coated in cadmium.
  From Quiz: Beneath Chicago
16 Elwood Blues listed this famous structure located at 1060 W. Addison as his place of residence on his driver's license in the movie "The Blues Brothers".
Answer: Wrigley Field

    Your options: [ The Wrigley Building ] [ Wrigley Field ] [ Comiskey Park ] [ Grant Park ]
  From Quiz: The Windy City
17 Where do "Da Bears play?
Answer: Soldier field

Many Chicagoans still incorrectly refer to it as Soldiers Field.
  From Quiz: My Kind Of Town, Chicago
18 This Hyde Park bar had five Ph.Ds tending bar once. You can also find the complete works of William Shakespeare and an encyclopedia.
Answer: Jimmy's Woodlawn Tap

Woodlawn Tap is a scruffy place, and has been for about 50 years. However, it attracts a diverse group of people from artists, construction workers, and University of Chicago students and professors. Jimmy passed away sadly in 1999
    Your options: [ Len's 48 ] [ Pacs Lounge ] [ Jimmy's Woodlawn Tap ] [ The Cove ]
  From Quiz: Absolute historic places in Chicago!
19 John G. Shedd was a stock boy who made his way to president of a Chicago department store. In 1924, he envisioned a salty and world-class scientific and educational museum to be called the Shedd what?
Answer: Aquarium

With over two million visitors a year, the (John G.) Shedd Aquarium is among the largest indoor aquariums in the world, exhibiting more than 8000 animals of 1,500 species in 80 habitats. The Abbott Oceanarium houses beluga whales, penguins and dolphins, and there is an impressive tank of Caribbean Reef sea life. You can walk through a recreation of the Amazon River, interact with a diver, or touch a stingray. In 1930, twenty railroad tank cars brought ocean water from Florida to fill the marine habitats. Sadly, John G. Shedd did not live to see the place open that year, but his daughters continued to foster his dream. Its unique design and architecture earned the aquarium the National Historic Landmark designation, as well as other awards.
  From Quiz: Chicago! Popeye's Magical Pizza City of Champions
20 Which film featured a suburban Chicago sculpture, "The Spindle", composed of eight cars skewered on a pole?
Answer: Wayne's World

Artist Dustin Shuler's sculpture, "The Spindle", was surrounded by twenty other sculptures that also incorporate cars in their design. These works of art were originally commissioned by the shopping center for the purpose of beautification. However, out of all Chicagoans, it may be that the local police department enjoyed "The Spindle" the most. Specifically, police rookies were often sent to the site to investigate an "eight car pileup".


The Spindle
Cermak Plaza
7043 Cermak Road
Berwyn, IL 60402


Once standing in Cermak Plaza "The Spindle" was dismantled when the shopping center was redeveloped. However, the top two cars of the artwork were retained for the construction of a new "Spindle".
    Your options: [ Nurse Betty ] [ Dumb and Dumber ] [ Wayne's World ] [ Weekend at Bernie's ]
  From Quiz: Windy City Wonders
21 These twin buildings are known to residents of Chicago as the Corn Cobs.
Answer: Marina City

Marina City was built in 1964 and is comprised of two twin 60-story buildings. Although not one of the most famous buildings in Chicago, it does mark Chicago as a city on the forward edge of modern urban architecture. It, like the John Hancock Center, is a multifunctional building with 18 stories of parking, apartments, shops, restaurants, banks, recreation facilities, and a theater.
    Your options: [ Merchandise Mart ] [ Marina City ] [ Navy Pier ] [ Museum of Science and Industry ]
  From Quiz: The Windy City
22 What is "Da Loop"?
Answer: Downtown

The Loop is the circular path taken by elevated trains around part of the downtown area.
  From Quiz: My Kind Of Town, Chicago
23 This famous bar goes back to the repeal of Prohibition.
Answer: Burwood Tap

Burwood Tap is nestled in the highly gentrified area of Lincoln Park. However, don't tell that to the deer head that sits above the bar along with the age old bar that predates the "yuppie" Lincoln Park attitude.
    Your options: [ Friar Tuck ] [ Butch McGuire's ] [ Burwood Tap ] [ Charleston ]
  From Quiz: Absolute historic places in Chicago!
24 If I live in Cicero near Austin and Roosevelt, and I want to get to O'Hare airport, how many train lines do I have to take?
Answer: 1

The Blue line is kind of shaped like a sideways U. It starts on the west side, heads east into downtown, curves north for a bit, and then heads out northwest to O'Hare.
  From Quiz: Riding the Rails on the CTA
25 One of the oldest zoos in the US, the Chicago Lincoln Park Zoo protects a massive "Quercus macrocarpa", which is what? Definitely its bark is worse than its bite.
Answer: Burr oak tree

Found in the Lincoln Park Zoo, the huge burr oak (Quercus macrocarpa) dates to 1830, before Chicago was founded. These native trees may live up to 400 years, grow over 100 ft (40 m) tall and be 10 ft (3 m) thick. It has a rugged bark, and is fire-resistant.

Opened in 1868, the zoo is free, open 365 days, and covers 35 acres (14 ha). It exhibits some 200 species, including big cats, polar bears, primates, reptiles, and penguins. In 2010, the zoo stopped housing elephants, to display endangered black rhinoceroses instead. Chicago's Brookfield Zoo is focused on conservation. The Barking Marsh Frog (Limnodynastes fletcheri), speaking of bark, is found in Australia.
    Your options: [ Sea lion ] [ Barking Marsh frog ] [ Native elephant ] [ Burr oak tree ]
  From Quiz: Chicago! Popeye's Magical Pizza City of Champions
26 In the late 1970s, Chicagoan Mitch Szewczyk began to decorate the exterior of his home with what items for protection and as a tribute to public figures he admired?
Answer: Crosses

Mitch Szewczyk, a devout Catholic, first hung one cross on his house to ward off local criminals. Perceiving cross power to be effective against crime, he later expanded his decorative activities to include the commemoration of those public individuals he found cross-worthy.


House of Crosses
1544 W. Chestnut Street
Chicago, IL 60622
  From Quiz: Windy City Wonders
27 The Great Fire of Chicago destroyed what major landmark, formerly located at the corner of Ontario Street and McClurg Court in the area now known as Streeterville? (Hint: remember the theme!)
Answer: Nothing--there was no land there during the Great Fire.

Until the 1830s, Lake Michigan came in as far west as what is now known as Michigan Avenue. By the time of the fire in 1871, a sandbar had built up around the pier but there wasn't much development on the sandy shore. The thriving area now known as Streeterville was built upon that sandbar and the huge amount of debris that was dumped into the lake during the post-fire cleanup.

Streeterville gets its name from George Streeter, a colorful fellow of the late 1800s who grafted his way into fraudulent ownership of most of the new lakefront property.
  From Quiz: Beneath Chicago
28 Is Jacques Cousteau your hero? At this site you can imagine you are him and explore the world beneath the waves.
Answer: The John G. Shedd Aquarium

The Shedd Aquarium is located in the Grant Park Complex and has several notable exhibits; the two most famous are the Caribbean Reef and the Oceanarium. The Caribbean Reef is a 90,000 gallon fish tank that houses over 70 species of fish, including rays and sharks. Here you can learn about several of the species while they are hand fed. The Oceanarium is a 3,000,000 gallon wonder that houses beluga whales and white-sided dolphins to name a couple of species.
  From Quiz: The Windy City
29 What was Riverview?
Answer: Amusement park

Every Chicago area kid went to Riverview at least once in their life to see Aladdin's Castle or ride the Giant Parachutes.
    Your options: [ Amusement park ] [ Neighborhood ] [ Skyscraper ] [ Restaurant ]
  From Quiz: My Kind Of Town, Chicago
30 Which Chicago classic has a stone Schlitz globe on its roof?
Answer: Bamboo Lounge

This neighborhood pub was originally built by the beer company in the 1920's.
    Your options: [ Bluestone ] [ Belmont Tavern ] [ Bamboo Lounge ] [ Benedict's Chicago ]
  From Quiz: Absolute historic places in Chicago!
31 Which line heads up through Evanston to serve Northwestern University?
Answer: Purple

I don't think it is a coincidence that this line is Purple - the Wildcats' colors are purple and white. During football season, the trains are always full of fans - happy and excited on their way to the game, and usually sad and dejected after the Cats lose. Ah, to make it to the Rose Bowl again, like in 1996.
    Your options: [ Yellow ] [ Purple ] [ Red ] [ Green ]
  From Quiz: Riding the Rails on the CTA
32 This Chicago observatory offers an all-round view from the 94th floor of one of the tallest buildings in the USA, the John Hancock Center. From where can you see some 80 miles (130 km) in any direction?
Answer: 360 Chicago

360 Chicago is an observation attraction on the 94th floor of the John Hancock Center skyscraper. An elevator takes you up about 1,000 feet (305 meters) in 40 seconds. There you find an 80-foot (24 m) wall of Chicago history, a multimedia tour, touchscreen information, and a magnificent view of downtown Chicago, the lakefront, and four adjoining states. 360 Chicago was voted "Best View in America" by "Travel and Leisure Magazine". The Space Needle and Top of the Rock are observation decks in other cities. Skydeck is another amazing observation deck in Chicago, from the 103rd floor of the Willis Tower.
  From Quiz: Chicago! Popeye's Magical Pizza City of Champions
33 What movie studio that produced films starring Charlie Chaplin, Gloria Swanson and Wallace Beery is located on W. Argyle Street in Chicago, IL?
Answer: Essanay Studios

Prior to Hollywood, CA becoming the film capital of the United States, a burgeoning film industry was established in Chicago, IL. Among the many studios was Essanay Studios, which produced such classics as "The Tramp" and "The Perils of Pauline" cliffhangers. This landmark has a distinctive pedimented entryway, graced on each side with paintings of war-bonneted Indian chiefs and carriage lanterns.


Essanay Studios
1345 W. Argyle Street
Chicago, IL 60640
  From Quiz: Windy City Wonders
34 This structure was originally intended for use in shipping and entertainment. It has seen many uses over the years, but as of 1994 it is almost exclusively used for entertainment.
Answer: Navy Pier

Built in 1916, Navy Pier was originally called Municipal Pier #2, and was built to support commercial shipping and also provide a venue for entertainment (theater etc.) During World War I and World War II it was used for military purposes, training mostly. Following the war it was the Chicago branch of the University of Illinois until it moved to its current location. After this period Navy Pier started to decay until refurbished into a vibrant entertainment center in 1994.
    Your options: [ Marina City ] [ Navy Pier ] [ Union Station ] [ Water Tower ]
  From Quiz: The Windy City
35 Eccentric Lar Daly unsuccessfully ran for mayor several times in Chicago. What was his nickname?
Answer: America First

Lar made seven unsuccessful runs for political office. He even ran for President in 1960!
  From Quiz: My Kind Of Town, Chicago
36 This famous south side Irish tap is located on Western Avenue.
Answer: Cork and Kerry

This is a little tough because there are so many bars on Western. But as I said you needed to be a true Chicagoan to play this quiz.
    Your options: [ Halligan Bar ] [ Casey's Corner ] [ Cork and Kerry ] [ Timothy O'Toole's ]
  From Quiz: Absolute historic places in Chicago!
37 Aside from the antique horse trough still in use at Water Tower Park, there is another on Michigan Avenue. At which cross street?
Answer: Chicago

The horse troughs used to belong to the fire department. They were to be torn out years after the fired department had switched to motor vehicles, but in the early seventies, carriage companies convinced the city to revive the old troughs and place them where their horses could use them.
    Your options: [ Superior ] [ Chicago ] [ Pearson ] [ Chestnut ]
  From Quiz: Carriage Horses in Chicago
38 A famous place to visit in Chicago is the Willis Tower, the tallest building in the world for 23 years. What was the original name of this lofty building?
Answer: Sears Tower

The Willis Tower, aka the Sears Tower, is a skyscraper of 108 floors. Sears, Roebuck and Company hired it built in 1970. From 1973 until 1996 it was the tallest building in the world. It is 1,450 feet (442 meters), and taller still when the antenna spire is counted. In 2009, the Willis Group (a global risk and insurance broker) bought the building and acquired rights to a new name.

On the 103rd floor is the famous observation Skydeck, 1,353 feet (412.4 m) above street level. From there you can see Chicago, and several surrounding states. In June of 2014 a camera captured the seconds when three of Chicago's tallest buildings were simultaneously hit by lightning during a severe storm.
  From Quiz: Chicago! Popeye's Magical Pizza City of Champions
39 Chicago's "Pillar of Fire" monument was erected in remembrance of the victims of what well-known disaster?
Answer: Great Chicago Fire

The Great Chicago Fire is no longer believed to have been started when Mrs. Catherine O'Leary's cow kicked over a lantern while being milked. In fact, the O'Leary's home was still standing after the fire was over. Therefore, the source of the fire remains unknown. What is known is that the fire began on October 8, 1871 and raged for 27 hours, resulting in the devastation of 3.5 square city miles. This disaster destroyed over 17,000 buildings, left one third of the population homeless, and killed 250 people. The haunting "Pillar of Fire" monument erected outside the fire department's training center stands in tribute to those 250 lives that the Great Chicago Fire claimed.


Pillar of Fire Monument
558 W. DeKoven Street
Chicago, IL 60607
  From Quiz: Windy City Wonders
40 What item underfoot during Chicago's Great Fire of 1871 has been blamed for helping the fire to spread in such a rapid and destructive way?
Answer: Wooden sidewalks and streets

Chicago was doomed by strong winds and the huge amount of wood in the city. Most buildings were made of wood. The ships in the harbor were all wood. The riverbanks were lined with lumberyards and coal yards. The raised wooden sidewalks, sealed with pitch and stuffed underneath with years of accumulated straw and debris, carried the fire down every street for miles.
  From Quiz: Beneath Chicago
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